6,8-Dihydroxy-5,7-dimethoxycoumarin

Details

• Internal ID: f9302164-abe9-46d4-bed4-f69622ac7eb5
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins
• IUPAC Name: 6,8-dihydroxy-5,7-dimethoxychromen-2-one
• SMILES (Canonical): COC1=C(C(=C(C2=C1C=CC(=O)O2)O)OC)O
• SMILES (Isomeric): COC1=C(C(=C(C2=C1C=CC(=O)O2)O)OC)O
• InChI: InChI=1S/C11H10O6/c1-15-9-5-3-4-6(12)17-10(5)8(14)11(16-2)7(9)13/h3-4,13-14H,1-2H3
• InChI Key: AXXSKWGVOIJTGN-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₆
• Molecular Weight: 238.19 g/mol
• Exact Mass: 238.04773803 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.22
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 167105-92-2
• 6,8-dihydroxy-5,7-dimethoxychromen-2-one
• 6,8-DIHYDROXY-5,7-DIMETHOXY-CHROMEN-2-ONE
• SCHEMBL17047860
• DTXSID00168230

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8773	87.73%
Caco-2	+	0.5148	51.48%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5566	55.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8934	89.34%
OATP1B3 inhibitior	+	0.8716	87.16%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7837	78.37%
P-glycoprotein inhibitior	-	0.8557	85.57%
P-glycoprotein substrate	-	0.9273	92.73%
CYP3A4 substrate	-	0.6322	63.22%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.5952	59.52%
CYP2C9 inhibition	-	0.8632	86.32%
CYP2C19 inhibition	-	0.7549	75.49%
CYP2D6 inhibition	-	0.7526	75.26%
CYP1A2 inhibition	+	0.7203	72.03%
CYP2C8 inhibition	-	0.8387	83.87%
CYP inhibitory promiscuity	+	0.5529	55.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6487	64.87%
Eye corrosion	-	0.9714	97.14%
Eye irritation	+	0.9069	90.69%
Skin irritation	-	0.6369	63.69%
Skin corrosion	-	0.9562	95.62%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7916	79.16%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.7073	70.73%
skin sensitisation	-	0.9147	91.47%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8387	83.87%
Acute Oral Toxicity (c)	III	0.5041	50.41%
Estrogen receptor binding	+	0.7442	74.42%
Androgen receptor binding	-	0.5698	56.98%
Thyroid receptor binding	-	0.6640	66.40%
Glucocorticoid receptor binding	+	0.5381	53.81%
Aromatase binding	+	0.5409	54.09%
PPAR gamma	+	0.7294	72.94%
Honey bee toxicity	-	0.9409	94.09%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8975	89.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.91%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.69%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.80%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.19%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.84%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.10%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	87.25%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.25%	89.00%

Plants that contains it

• Pelargonium sidoides

Cross-Links

• PubChem: 3025904
• LOTUS: LTS0249458
• wikiData: Q83037784